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4-Ethylaniline → N-(2',3',6'-trifluorophenyl)-4-ethylanilin

HRID 603339
Notes
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Reaction equation

HRID 603339 reaction equation
[CH2:1]([C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1)[CH3:2].[F:10][C:11]1[C:16]([F:17])=[CH:15][CH:14]=[C:13]([F:18])[C:12]=1Br.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[F:10][C:11]1[C:16]([F:17])=[CH:15][CH:14]=[C:13]([F:18])[C:12]=1[NH:7][C:6]1[CH:8]=[CH:9][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 115044-EthylanilineHCID 634876Binap, (A+-)-HCID 27364012-Bromo-1,3,4-trifluorobenzeneHCID 23676156Sodium t-butoxide

Product 1

HCID 57952161N-(2',3',6'-trifluorophenyl)-4-ethylanilinYield 86.3%

Reagents, catalysts & solvents 2

HCID 6505921
(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium
Catalyst
HCID 1140TolueneSolvent3×

Procedure

To a solution of 1.21 g of 4-ethylaniline, 1.10 g of 2,3,6-trifluoro-bromobenzene in 10 g of toluene is added consecutively 350 mg BINAP and 300 mg of bis-dibenzylideneaceton-palladium (0) [Pd(dba)2) in 3 ml of toluene and 0.9 g of sodium tert.-butoxide in 3 ml toluene. The mixture is flushed with nitrogen and heated for 6 h under reflux. After cooling to room temperature, water (30 ml), concentrated hydrochloric acid (10 ml) and hyflo (1 g) are added and stirring is continued for 1 h. The mixture is filtered and the filtrate is separated into its phases. The organic phase is washed three times with water, dried using magnesium sulfate and evaporated to dryness. The residue can be used as such in the following step or purified by flash chromatography on silica using toluene as the eluent affording 1.13 g of N-(2′,3′,6′-trifluorophenyl)-4-ethylanilin.

Workup

  1. customThe mixture is flushed with nitrogen
  2. temperatureheated for 6 h
  3. temperatureunder reflux
  4. additionwater (30 ml), concentrated hydrochloric acid (10 ml) and hyflo (1 g) are added
  5. filtrationThe mixture is filtered
  6. customthe filtrate is separated into its phases
  7. washThe organic phase is washed three times with water
  8. customdried
  9. customevaporated to dryness
  10. custompurified by flash chromatography on silica

Sources & evidence

ORD record
ord-438de11efc99464d80ed4cb71ffbe1fe
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07906677B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes